KR20050119192A - 치환된 피라졸 화합물 - Google Patents
치환된 피라졸 화합물 Download PDFInfo
- Publication number
- KR20050119192A KR20050119192A KR1020057018893A KR20057018893A KR20050119192A KR 20050119192 A KR20050119192 A KR 20050119192A KR 1020057018893 A KR1020057018893 A KR 1020057018893A KR 20057018893 A KR20057018893 A KR 20057018893A KR 20050119192 A KR20050119192 A KR 20050119192A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- pyrazol
- ylmethyl
- het
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 239000012453 solvate Substances 0.000 claims abstract description 25
- -1 ethyl- Chemical group 0.000 claims description 109
- 239000003814 drug Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 108020003175 receptors Proteins 0.000 claims description 8
- 102000005962 receptors Human genes 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- 101150065749 Churc1 gene Proteins 0.000 claims description 6
- 102100038239 Protein Churchill Human genes 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
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- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
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- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 claims 1
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims 1
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims 1
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- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 abstract description 4
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 10
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- JOAMPSTWYPZKOB-UHFFFAOYSA-N 1-[[1-[5-(4-fluorophenyl)pyridin-2-yl]-5-(furan-2-yl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=C(C=2OC=CC=2)N(C=2N=CC(=CC=2)C=2C=CC(F)=CC=2)N=C1 JOAMPSTWYPZKOB-UHFFFAOYSA-N 0.000 description 3
- SSPSLNRDCBBPFW-UHFFFAOYSA-N 1-cyclopentyl-4-[[1-[5-(4-fluorophenyl)pyridin-2-yl]-5-(furan-2-yl)pyrazol-4-yl]methyl]piperazine Chemical compound C1=CC(F)=CC=C1C1=CC=C(N2C(=C(CN3CCN(CC3)C3CCCC3)C=N2)C=2OC=CC=2)N=C1 SSPSLNRDCBBPFW-UHFFFAOYSA-N 0.000 description 3
- SXYMYEXTEQRESS-UHFFFAOYSA-N 1-ethyl-4-[[1-[5-(4-fluorophenyl)pyridin-2-yl]-5-(furan-2-yl)pyrazol-4-yl]methyl]piperazine Chemical compound C1CN(CC)CCN1CC1=C(C=2OC=CC=2)N(C=2N=CC(=CC=2)C=2C=CC(F)=CC=2)N=C1 SXYMYEXTEQRESS-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/40—Acylated on said nitrogen atom
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Landscapes
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- Plural Heterocyclic Compounds (AREA)
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| DE10315569.4 | 2003-04-05 | ||
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| DE10315572A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315573A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315571A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| EP1670460B1 (en) * | 2003-10-10 | 2014-11-26 | Bristol-Myers Squibb Company | Pyrazole derivatives as cannabinoid receptor modulators |
| MX2008000141A (es) | 2005-06-27 | 2008-04-07 | Exelixis Inc | Moduladores de lxr basados en imidazol. |
| JP2008169191A (ja) * | 2006-02-20 | 2008-07-24 | Eisai R & D Management Co Ltd | 運動ニューロン疾患治療剤 |
| EP2004627A2 (en) * | 2006-04-10 | 2008-12-24 | Arena Pharmaceuticals, Inc. | 3-pyridinyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| EP2121621B1 (en) | 2006-12-08 | 2014-05-07 | Exelixis Patent Company LLC | Lxr and fxr modulators |
| WO2010080864A1 (en) * | 2009-01-12 | 2010-07-15 | Array Biopharma Inc. | Piperidine-containing compounds and use thereof |
| JP5722891B2 (ja) | 2010-07-15 | 2015-05-27 | 大日本住友製薬株式会社 | ピラゾール化合物 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
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| US4146721A (en) * | 1969-09-12 | 1979-03-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrazol-4-acetic acid compounds |
| CH518155A (de) | 1970-08-18 | 1972-01-31 | Schaerer Willy | Verfahren zur Erleichterung des Schleifens schraubenlinienförmiger Nuten, bei einer Serie von unter sich gleichen Werkstücken mit je mindestens einer schraubenlinienförmig eingefrästen Nut und Simuliergerät zur Durchführung des Verfahrens |
| BE793955A (fr) * | 1972-01-15 | 1973-07-12 | Merck Patent Gmbh | Arylpiperazines et leur procede de preparation |
| DE2258033A1 (de) | 1972-11-27 | 1974-05-30 | Merck Patent Gmbh | Verfahren zur herstellung von pyrazolderivaten |
| DE2906252A1 (de) | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4631343A (en) * | 1983-11-07 | 1986-12-23 | Eli Lilly And Company | Cyanopyrazole intermediates |
| JPH089599B2 (ja) * | 1988-08-02 | 1996-01-31 | 三井東圧化学株式会社 | ピラゾールカルボン酸類の製造方法 |
| DE4425146A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| DE59508281D1 (de) | 1994-08-06 | 2000-06-08 | Merck Patent Gmbh | Benzolderivate und flüssigkristallines medium |
| NZ305799A (en) * | 1995-04-20 | 1999-01-28 | Searle & Co | Cyclic amidino agents useful as nitric oxide synthase inhibitors |
| JPH09227555A (ja) * | 1996-02-16 | 1997-09-02 | Taisho Pharmaceut Co Ltd | チエニルピラゾール誘導体 |
| ES2213892T3 (es) | 1997-01-21 | 2004-09-01 | Smithkline Beecham Corporation | Nuevos moduladores del receptor de canabinoides. |
| US6150393A (en) | 1998-12-18 | 2000-11-21 | Arena Pharmaceuticals, Inc. | Small molecule modulators of non-endogenous, constitutively activated human serotonin receptors |
| US20010044445A1 (en) * | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| US6632815B2 (en) * | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| AU1445001A (en) * | 1999-10-29 | 2001-05-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Process of making substituted pyrazoles |
| DE60017446T2 (de) * | 1999-11-05 | 2006-03-02 | Smithkline Beecham P.L.C., Brentford | Isochinolin- und Chinazolinderivate mit kombinierter 5-HT1A-, 5-HT1B- und 5-HT1D- Rezeptoraffinität |
| CA2440211A1 (en) * | 2001-03-09 | 2002-09-19 | Pfizer Products Inc. | Benzimidazole anti-inflammatory compounds |
| CA2450167A1 (en) * | 2001-06-12 | 2002-12-19 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| US20030130199A1 (en) * | 2001-06-27 | 2003-07-10 | Von Hoersten Stephan | Dipeptidyl peptidase IV inhibitors and their uses as anti-cancer agents |
| DE10149370A1 (de) | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| GR1004118B (el) | 2001-10-11 | 2003-01-21 | Μαρκος Νινολακης | Ηλεκτροχημικη μεθοδος υγρης οξειδωσης-αποστειρωσης υγρων αποβλητων απο σφαγεια ψαριων |
| MXPA04009352A (es) * | 2002-04-18 | 2005-01-25 | Pharmacia Corp | Terapia de combinacion para el tratamiento de la enfermedad de parkinson con inhibidores de ciclooxigenasa-2 (cox2). |
| US20060148858A1 (en) | 2002-05-24 | 2006-07-06 | Tsuyoshi Maekawa | 1, 2-Azole derivatives with hypoglycemic and hypolipidemic activity |
| AU2003262023A1 (en) | 2002-09-10 | 2004-04-30 | Takeda Pharmaceutical Company Limited | Five-membered heterocyclic compounds |
| AU2003287965A1 (en) | 2002-10-24 | 2004-05-13 | Carex Sa | Modulation of peroxisome proliferator activated receptors activity |
| DE10315571A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315573A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315572A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| US20070093492A1 (en) * | 2004-03-09 | 2007-04-26 | Weir-Torn Jiaang | Pyrrolidine derivatives |
-
2003
- 2003-04-05 DE DE2003115569 patent/DE10315569A1/de not_active Withdrawn
-
2004
- 2004-03-10 KR KR1020057018893A patent/KR20050119192A/ko not_active Withdrawn
- 2004-03-10 DE DE502004004089T patent/DE502004004089D1/de not_active Expired - Lifetime
- 2004-03-10 WO PCT/EP2004/002453 patent/WO2004089932A1/de not_active Ceased
- 2004-03-10 PL PL377604A patent/PL377604A1/pl unknown
- 2004-03-10 CA CA002521227A patent/CA2521227A1/en not_active Abandoned
- 2004-03-10 MX MXPA05010650A patent/MXPA05010650A/es not_active Application Discontinuation
- 2004-03-10 JP JP2006504620A patent/JP4740117B2/ja not_active Expired - Fee Related
- 2004-03-10 EP EP04718926A patent/EP1611122B1/de not_active Expired - Lifetime
- 2004-03-10 US US10/552,064 patent/US7842695B2/en not_active Expired - Fee Related
- 2004-03-10 ES ES04718926T patent/ES2287710T3/es not_active Expired - Lifetime
- 2004-03-10 CN CNA2004800086030A patent/CN1768052A/zh active Pending
- 2004-03-10 BR BRPI0408986-3A patent/BRPI0408986A/pt not_active Application Discontinuation
- 2004-03-10 AT AT04718926T patent/ATE364601T1/de not_active IP Right Cessation
- 2004-04-02 AR ARP040101117A patent/AR043835A1/es unknown
-
2005
- 2005-11-03 ZA ZA200508923A patent/ZA200508923B/xx unknown
-
2011
- 2011-02-28 JP JP2011041150A patent/JP2011153144A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011153144A (ja) | 2011-08-11 |
| MXPA05010650A (es) | 2005-12-12 |
| CN1768052A (zh) | 2006-05-03 |
| EP1611122B1 (de) | 2007-06-13 |
| ATE364601T1 (de) | 2007-07-15 |
| ZA200508923B (en) | 2007-02-28 |
| WO2004089932A1 (de) | 2004-10-21 |
| CA2521227A1 (en) | 2004-10-21 |
| JP4740117B2 (ja) | 2011-08-03 |
| PL377604A1 (pl) | 2006-02-06 |
| ES2287710T3 (es) | 2007-12-16 |
| DE10315569A1 (de) | 2004-10-14 |
| US20070010531A1 (en) | 2007-01-11 |
| DE502004004089D1 (de) | 2007-07-26 |
| AR043835A1 (es) | 2005-08-17 |
| BRPI0408986A (pt) | 2006-03-28 |
| EP1611122A1 (de) | 2006-01-04 |
| AU2004228124A1 (en) | 2004-10-21 |
| JP2006522039A (ja) | 2006-09-28 |
| US7842695B2 (en) | 2010-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20051004 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |